InChI=1S/C37H66N7O18P3S/c1-37(2,32(49)35(50)40-18-17-27(46)39-19-21-66-28(47)16-14-12-10-8-6-4-3-5-7-9-11-13-15-20-45)23-59-65(56,57)62-64(54,55)58-22-26-31(61-63(51,52)53)30(48)36(60-26)44-25-43-29-33(38)41-24-42-34(29)44/h24-26,30-32,36,45,48-49H,3-23H2,1-2H3,(H,39,46)(H,40,50)(H,54,55)(H,56,57)(H2,38,41,42)(H2,51,52,53)/t26-,30-,31-,32+,36-/m1/s1 |
ROZGNNDROQHXPF-BBECNAHFSA-N |
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCCO |
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Arabidopsis thaliana
(NCBI:txid3702)
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See:
PubMed
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acyl donor
Any donor that can transfer acyl groups between molecular entities.
(via acyl-CoA )
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plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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View more via ChEBI Ontology
3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-4-{[3-({2-[(16-hydroxyhexadecanoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphate}
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16-hydroxyhexadecanoyl-coenzyme A
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ChEBI
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16-hydroxypalmitoyl-CoA
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ChEBI
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16-hydroxypalmitoyl-coenzyme A
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ChEBI
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11195626
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Reaxys Registry Number
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Reaxys
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Kim SS, Grienenberger E, Lallemand B, Colpitts CC, Kim SY, Souza Cde A, Geoffroy P, Heintz D, Krahn D, Kaiser M, Kombrink E, Heitz T, Suh DY, Legrand M, Douglas CJ (2010) LAP6/POLYKETIDE SYNTHASE A and LAP5/POLYKETIDE SYNTHASE B encode hydroxyalkyl α-pyrone synthases required for pollen development and sporopollenin biosynthesis in Arabidopsis thaliana. The Plant cell 22, 4045-4066 [PubMed:21193570] [show Abstract] Plant type III polyketide synthases (PKSs) catalyze the condensation of malonyl-CoA units with various CoA ester starter molecules to generate a diverse array of natural products. The fatty acyl-CoA esters synthesized by Arabidopsis thaliana ACYL-COA SYNTHETASE5 (ACOS5) are key intermediates in the biosynthesis of sporopollenin, the major constituent of exine in the outer pollen wall. By coexpression analysis, we identified two Arabidopsis PKS genes, POLYKETIDE SYNTHASE A (PKSA) and PKSB (also known as LAP6 and LAP5, respectively) that are tightly coexpressed with ACOS5. Recombinant PKSA and PKSB proteins generated tri-and tetraketide α-pyrone compounds in vitro from a broad range of potential ACOS5-generated fatty acyl-CoA starter substrates by condensation with malonyl-CoA. Furthermore, substrate preference profile and kinetic analyses strongly suggested that in planta substrates for both enzymes are midchain- and ω-hydroxylated fatty acyl-CoAs (e.g., 12-hydroxyoctadecanoyl-CoA and 16-hydroxyhexadecanoyl-CoA), which are the products of sequential actions of anther-specific fatty acid hydroxylases and acyl-CoA synthetase. PKSA and PKSB are specifically and transiently expressed in tapetal cells during microspore development in Arabidopsis anthers. Mutants compromised in expression of the PKS genes displayed pollen exine layer defects, and a double pksa pksb mutant was completely male sterile, with no apparent exine. These results show that hydroxylated α-pyrone polyketide compounds generated by the sequential action of ACOS5 and PKSA/B are potential and previously unknown sporopollenin precursors. |
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